Hometown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $750 when you book a flight and hotel together*
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Your Hometown Vacation
An easy way to experience this city is with a customized Hometown vacation package. Base yourself in the neighborhood of The Loop, which is great for bars and pubs, history and festivals or go someplace else — our package deals are all about you. Eager to venture out and explore? SeatGeek Stadium, Chicago Ridge Shopping Mall and Trinity Christian College are just a few of the most popular places to visit during your trip to Hometown. Browse Expedia's wide range of travel options and start organizing your ultimate vacation to Hometown today.
Top Hometown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was CA $1,524, price is now CA $1,030 per person
CA $1,030
per person
Jun 11 - Jun 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (327 reviews)
The staff provided Excellent customer service!!
Reviewed on Apr 25, 2026
La Banque Hotel
Price was CA $1,779, price is now CA $1,190 per person
CA $1,190
per person
Jun 11 - Jun 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (480 reviews)
The staff was friendly and the bed was very comfortable! Easy to find parking, many food options within walking distance.
Reviewed on Apr 21, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,254, price is now CA $1,578 per person
CA $1,578
per person
Jun 4 - Jun 7
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,853 reviews)
The Trump Hotel was located in the best center place possible in the heart of Downtown Chicago, walkable distance to literally everything, bars, restaurants, tourist attractions, walk by the river and boat tours, magnificent mile, millennium park and the bean, the willis skydeck... it's also Super clean! Fresh nice smell in the hallways and the rooms. Lake view room had the entire Downtown and the lake view covered. Super amazing!!!! Amenities top notch. Very polite and friendly staff. Terrace 16 was a little slow but amazing food and ambiance. Highly recommended!
Reviewed on Apr 24, 2026
The Emily Hotel
Downtown Chicago
Price was CA $1,813, price is now CA $1,276 per person
CA $1,276
per person
Jun 10 - Jun 14
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Room was cozy, clean, comfortable! Staff very friendly and in great location
Reviewed on Apr 25, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was CA $1,879, price is now CA $1,353 per person
CA $1,353
per person
Jun 10 - Jun 14
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,348 reviews)
Conveniently located, cute bars and restaurants nearby and within walking distance of a tour bus stop. The room was clean, comfortable beds and the staff was pleasant.
Reviewed on Apr 22, 2026
Hometown Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from May 8 to May 9
CA $182
CA $217 total
May 8 - May 9
includes taxes & fees
8/10 Very Good! (10,145 reviews)
A family emergency came up that shortly after booking prevented me from being able to attend at all. Expedia approved for a full refund and needing the hotel's acceptance reached out in multiple ways including an email requesting acceptance of such but we have not heard back and it is now the next ...
Reviewed on Apr 26, 2026
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Apr 28 to Apr 29
CA $119
CA $181 total
Apr 28 - Apr 29
includes taxes & fees
8.2/10 Very Good! (2,643 reviews)
Staff was so kind and great!
Reviewed on Apr 26, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from May 25 to May 26
CA $161
CA $192 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,133 reviews)
Wish they had a mini fridge
Reviewed on Apr 26, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Hometown
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Hometown
Skydeck - Willis Tower Admission
CA $61
per adult
96% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
